Patent GB-700366-A (GB)
Title: New products having valuable plasticising properties and plastic compositions formed therewith
IPC: C07C43/11
Filed: 1950-12-19
Abstract: Polyvinyl and cellulose derivative plastic compositions contain as plasticizer at least one compound of the formula C10H7CH2 (OC2H4)x (OC3H6)y OR, where the naphthalene nucleus may be attached in the 1- or 2-position, x and y are zero or integers, the total of x + y being 1-4, and R is hydrogen or alkyl or acyl of 1-10 carbon atoms; the ethylene and propylene residues may not be in the order shown. Preferred plasticizers are:-for polyvinyl chloride, R = alkyl or acyl; for cellulose acetate, R=H; for cellulose nitrate, R = acyl. Thus polyvinyl chloride stabilized with lead stearate is plasticized with one of the following:-dipropylene glycol mono-a -naphthylmethyl mono - n - butyl ether, dipropylene glycol mono - a  - naphthylmethyl ether monoacetate, triethylene glycol mono - a  - naphthylmethyl mono - n - butyl ether, triethylene glycol mono - a  - naphthyl - methyl ether monoacetate, diethylene glycol mono - a  - naphthylmethyl mono - n - butyl ether, diethylene glycol mono-a  - naphthylmethyl ether monoacetate, triethylene glycol mono-a -naphthylmethyl ether mono - n - octyl ether and ethylene - propylene-diglycol mononaphthylmethyl ether mono-acetate; dibutyl phthalate may be added.  Cellulose acetate may be plasticized with triethylene glycol mono-a -naphthylmethyl ether or with a mixture of triethylene glycol mono - a  - naphthylmethyl ether mono - acetate and dimethyl phthalate.ALSO:The invention comprises ethylene, propylene, and ethylene propylene glycol mono-naphthylmethyl ethers of the formula <FORM:0700366/IV(b)/1> , where x and y are zero or integers, the total of x + y being 1-4, R is hydrogen or alkyl or acyl of 1-10 carbon atoms; the ethylene and propylene residues may not be in the order shown. Compounds (R = H) are made from chloromethyl-naphthalene by (1) reaction with the appropriate glycol(s) in the presence of an alkaline catalyst; (2) reaction with the alkali metal derivative of the appropriate glycol(s), or (3) alkaline hydrolysis to naphthyl carbinol and treatment with ethylene and/or propylene oxide in the presence of an alkaline catalyst.  Compounds (R = alkyl) are prepared by (1) reacting chloromethyl-naphthalene with the appropriate glycol ether, (2) etherifying the compounds (R = H) with a primary alkyl halide, or (3) etherifying with a b -haloethyl ether of a glycol or diglycol, provided that (x + y) does not exceed 4.  Compounds (R = acyl) are made by normal esterification with an acid, acid halide or anhydride.  In the examples, (1) a -chloromethylnaphthalene is heated with triethylene glycol and caustic potash; (2) the product of (1) is acetylated; (3) a -chloromethylnaphthalene is heated with diethylene glycol mono-n-butyl ether and caustic potash; (4) as in (3) using the n-octyl ether; (5) a -chloromethylnaphthalene is heated with dipropylene glycol and caustic potash; (6) the product of (5) is heated with n-butyl bromide and caustic potash; (7) diethylene glycol mono-a -naphthylmethyl ether is heated with b -chloro-b 1-ethoxy-diethylether and caustic potash; (8) a -naphthyl carbinol is reacted with ethylene oxide and caustic soda and the product fractionated; (9) a -chloromethylnaphthalene is heated with diethylene glycol and caustic potash; (10) the product of (9) is acetylated; (11) a -chloromethylnaphthalene is reacted with the sodium derivative of ethylene glycol; (12) a mixture of a - and b -chloromethylnaphthalenes (see Specification 633,097) is heated with the potassium derivative of hydroxypropoxyethanol (from ethylene glycol and propylene oxide) and the product acetylated.  The b -compounds corresponding to Examples 1-11 may be prepared similarly. Other specified products are dipropylene glycol mono-a -naphthylmethyl ether monoacetate and triethylene glycol mono-a -naphthylmethyl mono-n-butyl ether.